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Preparation method of N-tert-butyl oxycarbonyl alkyl guanidine

A technology of tert-butoxycarbonyl hydrocarbyl guanidine and bis-tert-butoxycarbonyl hydrocarbyl guanidine is applied in the field of preparation of N-tert-butoxycarbonyl hydrocarbyl guanidine, which can solve the problems of non-reaction and low yield of amine, and achieve less environmental pollution, Easy operation and mild reaction conditions

Inactive Publication Date: 2018-08-28
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the yield of amine with larger steric hindrance is very low, or even no reaction;

Method used

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  • Preparation method of N-tert-butyl oxycarbonyl alkyl guanidine
  • Preparation method of N-tert-butyl oxycarbonyl alkyl guanidine
  • Preparation method of N-tert-butyl oxycarbonyl alkyl guanidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: The method for preparing N-tert-butoxycarbonyl-(4-methoxybenzyl)guanidine, the specific operation is as follows:

[0017]

[0018] Add N,N'-bis-tert-butoxycarbonyl-(4-methoxybenzyl)guanidine (0.007mol) into a dry three-necked flask, dissolve it with 300mL isopropanol, add sodium methoxide (0.021mol), gradually Warm up to 82°C, reflux and stir the reaction. After TLC tracking for 8 hours, the raw material point disappears. The reaction is stopped and the solvent is spin-dried. The residue is dissolved in 100 mL of ethyl acetate, washed with water and saturated brine for three times, and dried over anhydrous sodium sulfate. After drying, the crude product was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 3:1 elution) to obtain 1.8 g of a colorless oily liquid, with a yield of 92%. 1 H NMR (300 MHz, CDCl 3 ) δ ppm 7.11(br s, 1H, NH), 6.80 (m, 2H, Ph), 6.77 (m, 2H, Ph), 4.83(m, 2H, CH 2 ), 4.25 (s, 3H, CH 3 ), 3.70(br s, 1H, NH), 1.95 (br...

Embodiment 2

[0019] Example 2: The method for preparing N-tert-butoxycarbonyl isopropylguanidine, the specific operation is as follows:

[0020]

[0021] Add N,N'-bis-tert-butoxycarbonyl isopropylguanidine (0.013mol) into a dry three-necked flask, dissolve it with 100mL methanol, add sodium hydroxide (0.026mol), gradually increase the temperature to 65°C, reflux and stir to react. After TLC tracking for about 9 hours, the raw material point disappeared, the reaction was stopped, and the solvent was spin-dried. The residue was dissolved in 100 mL ethyl acetate, washed with water and saturated brine three times, dried over anhydrous sodium sulfate and spin-dried to obtain a colorless oily liquid 2.1 g, HPLC purity 98%, yield: 81%; 1 H NMR (600 MHz, CDCl 3 )δ ppm 8.59 (br s, 1H, NH), 4.77 (m, 1H, CH), 2.48 (br s, 1H, NH), 1.94 (br s,1H, NH), 1.56 (s, 9H, (CH 3 ) 3 ), 1.19 (d, J =6.4 Hz, 6H, (CH 3 ) 2 ).

Embodiment 3

[0022] Example 3: The method for preparing N-tert-butoxycarbonylpropylguanidine, the specific operation is as follows:

[0023]

[0024] Add N,N'-bis-tert-butoxycarbonylpropylguanidine (0.009mol) into a dry three-necked flask, dissolve it with 100mL of tetrahydrofuran, add potassium hydroxide (0.054mol), gradually increase the temperature to 66°C, reflux and stir to react, TLC After tracking for about 3 hours, the raw material point disappeared, the reaction was stopped, the solvent was spin-dried, the residue was dissolved in 100 mL ethyl acetate, washed with water and saturated brine three times, dried over anhydrous sodium sulfate and spin-dried, the crude product passed through a silica gel column column After analysis (n-hexane: ethyl acetate = 3:1), 1.5 g of a yellowish oily liquid was obtained, with a yield of 83%; 1 H NMR (300 MHz, CDCl 3 ) δ ppm 7.19 (br s, 1H, NH), 4.17 (m,2H, CH 2 ), 2.91 (br s, 1H, NH), 2.01(br s, 1H, NH), 1.94 (d, 2H, J = 24.1Hz, CH 2 ), 1.18 (s, 9H...

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Abstract

The invention discloses a preparation method of N-tert-butyl oxycarbonyl alkyl guanidine. According to the method, easy-to-obtain N,N'-bis-tert-butyl oxycarbonyl alkyl guanidine is used as raw materials; under the solvent existence, alkali is used as a reagent for selective deprotection to eliminate one protection group so as to obtain the N-tert-butyl oxycarbonyl alkyl guanidine. The method provided by the invention has the characteristics that the reaction regent is cheap and can be easily obtained; the reaction conditions are mild; the selectivity is high; the operation process is simple; the post treatment is simple and convenient; the obtained product has high purity and high yield; the method is suitable for mass preparation, and the like. The prepared N-tert-butyl oxycarbonyl alkylguanidine can be used as a critical organic synthesis intermediate to be used for the synthesis of multifunctional compounds.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a preparation method of N-tert-butoxycarbonyl hydrocarbyl guanidine. Such compounds can be used as important organic synthesis intermediates for the synthesis of various functional compounds. Background technique [0002] Hydrocarbyl guanidine is a very important class of pharmaceutical and fine chemical intermediates with a wide range of applications. Due to its unique chemical structure and physical and chemical properties, guanidine compounds have been found to have a variety of pharmacological activities: antiviral, antibacterial, anti-inflammatory, treatment of malaria, diabetes, etc. The synthesis of guanidine compounds has therefore attracted much attention, and a large number of different guanidine synthesis methods have been reported. [0003] N-tert-butoxycarbonyl hydrocarbyl guanidine compounds, as key organic synthesis intermediates, have important app...

Claims

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Application Information

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IPC IPC(8): C07C277/08C07C279/24
CPCC07C277/08C07C279/24
Inventor 王月平钟鹏叶杨常捷杨朋何严萍
Owner KUNMING UNIV OF SCI & TECH